SYNTHESIS AND DIELS-ALDER REACTIONS OF HOMOCHIRAL 2-SULFINYLMALEATES WITH CYCLOPENTADIENE

被引:26
作者
ALONSO, I [1 ]
CID, MB [1 ]
CARRETERO, JC [1 ]
RUANO, JLG [1 ]
HOYOS, MA [1 ]
机构
[1] UNIV AUTONOMA MADRID CANTO BLANCO,DEPT QUIM C-I,E-28049 MADRID,SPAIN
关键词
D O I
10.1016/S0957-4166(00)80020-8
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Enantiomerically pure 2-p-tolylsulfinylmaleates 1, 2 and 3 have been readily prepared by Knoevenagel reaction between (S)-menthyl p-toluenesulfinate and glyoxylic acid. Their asymmetric Diels-Alder reactions with cyclopentadiene have been studied under a wide range of uncatalyzed and catalyzed conditions and the stereochemical results have been explained by assuming a steric control approach, in term of S-cis or S-trans favoured conformations. Uncatalyzed Diels-Alder reactions of 1 and some Lewis acid catalyzed Diels-Alder reactions of 2 show high facial and endo selectivities. The facial selectivity of dienophile 2 highly depends on the Lewis acid, whereas reactivity of 1 and 3 is very sensitive to the solvent. These sulfinylmaleates 1, 2 and 3 act as synthetic equivalents of chiral acetylenedicarboxylates in Diels-Alder reactions after basic elimination of the sulfinylic moiety in the resulting adducts.
引用
收藏
页码:1193 / 1207
页数:15
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